Heart of Chicago Vacations from $252

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Your Heart of Chicago Vacation

Experience everything this neighborhood has to offer with a customized Heart of Chicago vacation package. However you see yourself spending your time here, you'll find countless opportunities for fun, adventure and relaxation. When it's time to explore the sights, you'll find a lot of awesome attractions nearby including University of Illinois Chicago, United Center and Anna and Frederick Douglass Park. Visit one, two or all during your trip to Heart of Chicago. No matter your travel plans or the size of your budget, booking your dream Heart of Chicago vacation is easy with Expedia.

The Latest Heart of Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $412, price is now $252 per person
$252
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Love the staff here. Great stay all the way around! I was in 2409. Quiet room.

Reviewed on Dec 11, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $479, price is now $293 per person
$293
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
The rooms were great. Very spacious, fully stocked kitchen and extremely clean. We loved having access to the 8th floor with the steam room, sauna, fitness center, game rooms, and socializing areas 24/7. Would love to experience it in the summer with the pool and outdoor areas. We were also fortunate enough to attend during their Christmas Brunch buffet which was such a great perk! If the price stays around the same, I will continue to stay at Level hotels exclusively in any cities I visit that has one! I’ve already told so many people about my wonderful hotel experience.

Reviewed on Dec 9, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $699, price is now $434 per person
$434
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
All of the above. Staff was wonderful. Room was clean and comfortable. On site amenities were great and food was superb. Best espresso martini I’ve ever tasted.

Reviewed on Dec 11, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $423, price is now $275 per person
$275
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Concierge not helpful and neither is was the door man, Neither would get me a cab, they said to just stand outside

Reviewed on Dec 4, 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $454, price is now $295 per person
$295
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
Amazing location. Love this historic hotel and the included room service breakfast is one of the best I’ve ever had.

Reviewed on Dec 8, 2025

Where to stay in Heart of Chicago

Find the best Heart of Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Heart of Chicago
Downtown Chicago showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Heart of Chicago Hotel Deals

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $117 total per night from Dec 17 to Dec 18
$117 total
Dec 17 - Dec 18
Total with taxes and fees
8.4/10 Very Good! (5,361 reviews)
Everything was prefect. My only gripe was the heat was not heating as it should on 80 degrees. It was 20 degrees outside everyday. Other than that i will definitely return for another stay.. staff and Valetn were very professional and accommodating...10 star stay...

Reviewed on Dec 10, 2025

Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $95 total per night from Jan 5 to Jan 6
$95 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
8.8/10 Excellent! (3,456 reviews)
Clean room and friendly staff. We would definitely visit again.

Reviewed on Dec 10, 2025

Hilton Chicago/Magnificent Mile Suites
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $149 total per night from Jan 4 to Jan 5
$149 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.2/10 Wonderful! (2,109 reviews)
Awesome stay in an amazing room - lobby and bar/restaurant area were excellent as well. Location was perfect for our show at the CIBC Theatre nearby.

Reviewed on Dec 10, 2025

Silversmith Hotel Chicago Downtown
See all 4,847 properties in Heart of Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Heart of Chicago

Canalport Riverwalk Park

After visiting Canalport Riverwalk Park, make a plan to see the other sights and activities in Chicago. Experience the area's art scene and festivals.

Canalport Riverwalk Park

Mexican Fine Arts Center Museum

You can spend an afternoon studying the exhibits at Mexican Fine Arts Center Museum in Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.

Mexican Fine Arts Center Museum

Things to do

River tour boat in Chicago

Architecture River Tour

$54
per adult
96% of travellers recommend
Architecture River Tour
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$98
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$45
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.